alpha-Chloro-o-xylene → 2-[(2-Methylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 2053571

Reaction equation

HRID 2053571 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:10][C:9](=[S:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[CH3:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][S:18][C:9]1[NH:8][C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1

Participants

4

Reactant 2

HCID 11093alpha-Chloro-o-xyleneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685671662-[(2-Methylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-methylbenzyl chloride (0.204 mL, 1.57 mmol) in abs. EtOH (2 mL) is heated at 95° C. for 24 h. The reaction mixture is cooled to RT, evaporated to dryness, and the residue suspended in Et2O. The insoluble material is filtered to give 174 mg of the product 227. 1H NMR (DMSO-d6) δ 11.28 (s, 2H), 7.68 (m, 1H), 7.55-7.20 (m, 3H), 7.20-7.00 (m, 6H), 7.00-6.90 (m, 4H), 5.82 (s, 2H), 4.81 (s, 2H), 2.44 (s, 3H); MS: m/z 359 (M++1).

Workup

  1. customevaporated to dryness
  2. filtrationThe insoluble material is filtered

Sources & evidence

ORD record
ord-fedafde2ef7241dda5586f04b8742a94
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

Loading…